Water → HCID 58459156, compound

HRID 2036622Notes

Reaction equation

HRID 2036622 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[C:10]2[CH:18]([NH2:20])[CH3:19])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl[C:22]1[C:27]([C:28]#[N:29])=[CH:26][N:25]=[CH:24][N:23]=1.CC[N:32](C(C)C)C(C)C.O>C(O)CCC>[NH2:32][C:22]1[C:27]([C:28]#[N:29])=[C:26]([NH:20][CH:18]([C:10]2[N:9]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)[CH3:19])[N:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 131269094-Chloropyrimidine-5-carbonitrileHCID 58459390HCID 58459390, compound

Product 1

HCID 58459156HCID 58459156, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

1-(-(3,5-Difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine (600 mg, 2.18 mmol) and 4-chloro-pyrimidine-5-carbonitrile (300 mg, 2.18 mmol) were dissolved in n-butanol (30 mL). After the addition of DIPEA (422 mg, 3.28 mmol) the reaction mixture was heated at 120° C. overnight. The mixture was cooled to rt and water (50 mL) was added. The mixture was extracted with EtOAc (300 mL), dried over sodium sulfate and concentrated in vacuo to provide a crude product. The crude product was purified by column chromatography using 100-200 mesh silica gel and 0-50% EtOAc in hexane to provide 4-amino-6-(1-(3-(3,5-difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)-ethylamino)pyrimidine-5-carbonitrile: 1H NMR (400 MHz, DMSO-d6) δ 1.580 (d, J=6.8 Hz, 3H), 5.683-5.753 (m, 1H), 7.205 (br s, 2H), 7.307-7.367 (m, 4H), 7.768 (d, J=8 Hz, 1H), 7.888 (s, 1H), 8.149-8.172 (m, 1H), 8.276-8.292 (m, 1H); LC-MS (ESI) m/z 393.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionThe mixture was extracted with EtOAc (300 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto provide a crude product
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c75f981fafac4f82bee238afcec9529a
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

Loading…